Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and tembotrione and/or topramezone

ABSTRACT

Provided herein are herbicidal compositions and methods of controlling undesirable vegetation utilizing (a) a compound of formula (I): 
     
       
         
         
             
             
         
       
     
     or an agriculturally acceptable salt or ester thereof, and (b) tembotrione and/or topramezone. The compositions and methods provided herein provide control of undesirable vegetation, e.g., in corn crops such as field corn, field corn grown for seed, and popcorn, sweet corn, sorghum, and any other crops that are naturally tolerant to or contain herbicide tolerant traits to these active ingredients.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of U.S. Provisional Patent Application Ser. No. 62/543,504 filed Aug. 10, 2017, which is expressly incorporated by reference herein.

BACKGROUND

The protection of crops from weeds and other vegetation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use. However, there remains a need for compositions and methods that are effective in controlling undesirable vegetation.

SUMMARY

Described herein are herbicidal compositions comprising an herbicidally effective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester thereof, and (b) tembotrione and/or topramezone.

Additionally, methods of controlling undesirable vegetation including contacting the vegetation or the locus thereof, including but not limited to, soil or water, with a composition containing a herbicidally effective amount of (a) a compound of the formula (I) or an agriculturally acceptable salt or ester thereof, and (b) tembotrione and/or topramezone, to prevent the emergence or growth of vegetation, particularly undesirable vegetation are described herein.

In some embodiments, (a) and (b) can be provided together to furnish a herbicidal effect that is more than the additive effect of (a) and (b) when used separately.

DETAILED DESCRIPTION Definitions

As used herein, the compound of formula (I) is 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid and has the following structure:

Compounds of formula (I) are described in U.S. Pat. No. 7,314,849 B2, which is incorporated herein by reference in its entirety. Exemplary uses of the compound of the formula (I), which is also known as florpyrauxifen, include controlling undesirable vegetation, including grass, broadleaf and sedge weeds, in multiple non-crop and cropping situations.

Exemplary chemical forms of the compound of formula (I) include, but are not limited to, for example, the benzyl ester of the compound of formula (I) or benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate, which is also known as Rinskor™ Active and florpyrauxifen-benzyl, and has the following structure (II):

The benzyl ester of formula (II) is described in U.S. Pat. No. 8,883,688 B2, which is incorporated herein by reference in its entirety.

Without being limited to any theory, HPPD inhibitors are inhibitors of 4-hydroxyphenylpyruvate dioxygenase, an oxygenase involved in the creation of energy in plants and higher order eukaryotes. Exemplary HPPD inhibitors include, but are not limited to, tembotrione and topramezone.

As used herein, tembotrione, shown below, is 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-1,3-cyclohexanedione. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of tembotrione include its use for post-emergence control a wide range of dicotyledonous and monocotyledonous weed species in maize

As used herein, topramezone, shown below, is [3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of topramezone include its use for post-emergence weed control in maize.

The term herbicide, as used herein, means an active ingredient that kills, controls or otherwise adversely modifies the growth of plants. As used herein, a herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes a “herbicidal effect,”. i.e. an adversely modifying effect and includes deviations from natural development, killing, regulation, desiccation, retardation.

As used herein, controlling undesirable vegetation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and vegetation.

As used herein, plants and vegetation include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, and established vegetation.

As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity or that are or can be converted in plants, water, or soil to the referenced herbicide or active moiety. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending upon the pH, may be in the dissociated or undissociated form.

Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium, and aminium cations of the formula:

R¹R²R³R⁴N⁺

wherein R¹, R², R³ and R⁴ each, independently represents hydrogen or C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, C₃-C₁₂ alkynyl, or aryl, each of which is optionally substituted by one or more hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio or phenyl groups, provided that IV, R², R³ and R⁴ are sterically compatible. Additionally, any two of R¹, R², R³ and R⁴ together may represent an aliphatic difunctional moiety containing one to twelve carbon atoms and up to two oxygen or sulfur atoms. Salts can be prepared by treatment with a metal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methyl-thiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tetramethylammonium hydroxide or choline hydroxide.

Exemplary esters include those derived from C₁-C₁₂, alkyl, C₃-C₁₂ alkenyl, C₃-C₁₂ alkynyl or C₇-C₁₀ aryl-substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or unsubstituted or substituted benzyl alcohols. Benzyl alcohols may be substituted with from 1-3 substituents independently selected from halogen, C₁-C₄ alkyl or C₁-C₄ alkoxy. Esters can be prepared by coupling of the acids with the alcohol using any number of suitable activating agents such as those used for peptide couplings such as dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by reacting the acids with alkylating agents such as alkylhalides or alkylsulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the corresponding acid chloride of an acid with an appropriate alcohol; by reacting the corresponding acid with an appropriate alcohol in the presence of an acid catalyst or by transesterification.

Compositions

Provided herein are herbicidal compositions comprising a herbicidally effective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester of thereof, and (b) tembotrione and/or topramezone.

Provided herein are also methods of controlling undesirable vegetation comprising contacting the vegetation or the locus thereof, i.e., area adjacent to the plant, with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of the compound of formula (I), or an agriculturally acceptable salt or ester thereof, and (b) tembotrione or topramezone. In certain embodiments, the methods employ the compositions described herein.

The combination of a compound of formula (I), or an agriculturally acceptable salt or ester thereof, and tembotrione and/or topramezone, can exhibit herbicidal activity such that the herbicidal active ingredients are more effective in combination than when applied individually.

In some embodiments, the activity of the herbicidal compositions described herein is greater than the sum of the activity of the individual active ingredients in the compositions.

Herbicidal activity is exhibited by the herbicidal compositions described herein when they are applied pre- and post-emergence directly to a plant or to the locus of the plant at any stage of growth. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, the amount of chemical applied, and combinations thereof. These and other factors can be adjusted to promote non-selective or selective herbicidal action. The compositions described herein can be applied as a post-emergence application, pre-emergence application, or in-water application to flooded paddy rice or water bodies (e.g., ponds, lakes and streams), to relatively immature to mature undesirable vegetation to achieve the maximum control of weeds.

The compound of formula (I), or a salt or ester thereof, and tembotrione and/or topramezone, can be used in combination with herbicides that are selective for the crop being treated and complement the spectrum of weeds controlled by these compounds at the application rate employed. The compositions described herein and other complementary herbicides can be applied at the same time, either as a combination formulation, as a tank-mix, or as sequential applications.

The present compositions can be applied to vegetation or the soil or water adjacent thereto by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.

The concentration of active ingredients in the compositions described herein is generally from 0.0005 to 98 percent by weight. Alternatively, the concentration can be from 0.0006 to 90 percent by weight. In compositions designed to be employed as concentrates, the active ingredients can be present in a concentration from 0.1 to 98 weight percent, or from about 0.5 to 90 weight percent. Such compositions can be diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds can contain about 0.0006 to 15.0 weight percent or from 0.001 to 10.0 weight percent active ingredient.

In the compositions and methods described herein, the weight ratio of the compound of formula (I), or a salt or ester thereof, to the tembotrione on a gram active ingredient per hectare (g ai/ha) basis is within the range of from 1:200 to 200:1. The weight ratio of the compound of formula (I), or a salt or ester thereof, to tembotrione on a gram active ingredient per hectare (g ai/ha) basis also can be within the range from 1:175 to 175:1, 1:150 to 150:1, 1:125 to 125:1, 1:100 to 100:1, 1:90 to 90:1, 1:80 to 80:1, 1:70 to 70:1, 1:60 to 60:1, 1:50 to 50:1, 1:50 to 40:1, 1:50 to 30:1, 1:50 to 20:1, 1:50 to 10:1, 1:40 to 40:1, 1:30 to 30:1, 1:20 to 20:1, 1:20 to 10:1, 1:20 to 5:1, 1:20 to 3:1, 1:10 to 10:1, 1:5 to 5:1, and from 1:3 to 3:1.

In the compositions and methods described herein, the weight ratio of the compound of formula (I), or a salt or ester thereof, to topramezone on a gram active ingredient per hectare (g ai/ha) basis is within the range from 1:200 to 200:1. The weight ratio of the compound of formula (I), or a salt or ester thereof, to topramezone on a gram active ingredient per hectare (g ai/ha) basis also can be within the range from 1:175 to 175:1, 1:150 to 150:1, 1:125 to 125:1, 1:100 to 100:1, 1:90 to 90:1, 1:80 to 80:1, 1:70 to 70:1, 1:60 to 60:1, 1:50 to 50:1, 1:50 to 40:1, 1:50 to 30:1, 1:50 to 20:1, 1:40 to 40:1, 1:30 to 30:1, 1:20 to 20:1, 1:10 to 10:1, 1:10 to 5:1, 1:5 to 5:1, and from 1:3 to 3:1.

The application rate will depend upon the particular type of weed to be controlled, the degree of control required, and the timing and method of application. In the compositions described herein the compound of formula (I), or a salt or ester thereof, can be applied at an application rate of from 1 gram active ingredient per hectare (g ai/ha) to 200 g ai/ha based on the total amount of the compound of formula (I), or a salt or ester thereof, in the composition. Additionally, in the compositions described herein the compound of formula (I), or a salt or ester thereof, can be applied at an application rate of from 1.25 gr ai/ha to 190 gr ai/ha, 1.5 g ai/ha to 150 gr ai/ha, 1.75 g ai/ha to 125 g ai/ha, 2 g ai/ha to 100 g ai/ha, 2.5 g ai/ha to 75 g ai/ha, 3 g ai/ha to 55 g ai/ha, 3.5 g ai/ha to 50 g ai/ha, 5 g ai/ha to 40 g ai/ha, 5.5 g ai/ha to 45 g ai/ha, 6 g ai/ha to 40 g ai/ha, 7 g ai/ha to 35 g ai/ha, 1 g ai/ha to 35 g ai/ha, 1 g ai/ha to 30 g ai/ha, 1 g ai/ha to 25 g ai/ha, 2 g ai/ha to 20 g ai/ha, 2.5 g ai/ha to 10 g ai/ha or 5 g ai/ha to 10 g ai/ha based on the total amount of the compound of formula (I) or a salt or ester thereof in the composition.

In the compositions described herein the tembotrione can be applied at an application rate of from 1 g ai/ha to 200 g ai/ha. Additionally, in the compositions described herein the tembotrione can be applied at an application rate of from 1 g ai/ha to 175 g ai/ha, 1 g ai/ha to 150 g ai/ha, 1 g ai/ha to 125 g ai/ha, 1 g ai/ha to 100 g ai/ha, 1 g ai/ha to 90 g ai/ha, 1 g ai/ha to 80 g ai/ha, 1 g ai/ha to 60 g ai/ha, 2 g ai/ha to 150 g ai/ha, 2 g ai/ha to 100 g ai/ha, 2 g ai/ha to 75 gr ai/ha, 25 g ai/ha to 190 g ai/ha, 25 g ai/ha to 150 g ai/ha, 25 g ai/ha to 125 g ai/ha, 25 g ai/ha to 120 g ai/ha, 25 g ai/ha to 110 g ai/ha, 25 g ai/ha to 100 g ai/ha, 25 g ai/ha to 90 g ai/ha, 25 g ai/ha to 80 g ai/ha, 25 g ai/ha to 70 g ai/ha, 25 g ai/ha to 60 g ai/ha, 25 g ai/ha to 50 g ai/ha, 30 g ai/ha to 120 g ai/ha, 30 g ai/ha to 110 g ai/ha, 30 g ai/ha to 100 g ai/ha, 30 g ai/ha to 90 g ai/ha, 30 g ai/ha to 80 g ai/ha, or 30 g ai/ha to 60 g ai/ha based on the total amount of the tembotrione in the composition. For example, tembotrione can be applied at a rate from 2 g ai/ha to 200 g ai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from 1 g ai/ha to 200 g ai/ha.

Additionally, in the compositions described herein the topramezone can be applied at an application rate of from 1 g ai/ha to 200 g ai/ha. Additionally, in the compositions described herein the topramezone can be applied at an application rate of from 1 g ai/ha to 190 g ai/ha, 1 g ai/ha to 180 g ai/ha, 1 g ai/ha to 170 g ai/ha, 1 g ai/ha to 160 g ai/ha, 1 g ai/ha to 150 g ai/ha, 1 g ai/ha to 140 g ai/ha, 1 g ai/ha to 130 g ai/ha, 1 g ai/ha to 120 g ai/ha, 1 g ai/ha to 110 g ai/ha, 1 g ai/ha to 90 g ai/ha, 1 g ai/ha to 80 g ai/ha, 1 g ai/ha to 70 g ai/ha, 1 g ai/ha to 60 g ai/ha, 1 g ai/ha to 50 g ai/ha, 1 g ai/ha to 40 g ai/ha, 1 g ai/ha to 30 g ai/ha, 1 g ai/ha to 20 g ai/ha, 1 g ai/ha to 10 g ai/ha, 1 g ai/ha to 5 g ai/ha, 2 g ai/ha to 50 g ai/ha, 2 g ai/ha to 45 g ai/ha, 2 g ai/ha to 40 g ai/ha, 2 g ai/ha to 30 g ai/ha, 2 g ai/ha to 20 g ai/ha, 2 g ai/ha to 10 g ai/ha, 2 g ai/ha to 5 g ai/ha, 5 g ai/ha to 50 g ai/ha, 5 g ai/ha to 45 g ai/ha, 5 g ai/ha to 40 g ai/ha, 5 g ai/ha to 30 g ai/ha, 5 g ai/ha to 20 g ai/ha, or 5 g ai/ha to 10 g ai/ha based on the total amount of the topramezone in the composition. For example, topramezone can be applied at a rate from 2 g ai/ha to 200 g ai/ha and the compound of formula (I) or a salt or ester thereof is applied at a rate from 1 g ai/ha to 200 g ai/ha.

The mixtures described herein can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, tank-mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the compositions and methods described herein include, but are not limited to: 4-CPA, 4-CPB, 4-CPP, 3,4-DA, 2,4-DB, 3,4-DB, 3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazon, benthiocarb, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole, chlorprocarb, carfentrazone (e.g., carfentrazone-ethyl), CDEA, CEPC, chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon (e.g., cinidon-ethyl), cinmethylin, cinosulfuron, cisanilide, clacyfos, clethodim, cliodinate, clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop (e.g., cyhalofop-butyl), cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethbenzamide, ethalfluralin, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop (e.g., fenoxaprop-P-ethyl), fenoxaprop-P-ethyl+isoxadifen-ethyl, fenoxasulfone, fenquinotrione, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop (e.g., fluazifop-P-butyl), fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr (e.g., flufenpyr-ethyl), flumetsulam, flumezin, flumiclorac (e.g., flumiclorac-pentyl), flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen, halauxifen, halauxifen-methyl, halosafen, halosulfuron (e.g., halosulfuron-methyl), haloxydine, haloxyfop-methyl, haloxyfop-P (e.g., haloxyfop-P-methyl), hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lancotrione, lactofen, lenacil, linuron, MAA, MAMA, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham (e.g., phenmedipham-ethyl), phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron (e.g., primisulfuron-methyl), procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, prohexadione-calcium, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen (e.g., pyraflufen-ethyl), pyrasulfotole, pyrazogyl, pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tiocarbazil, tioclorim, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron (e.g., tribenuron-methyl), tricamba, triclopyr (e.g., triclopyr choline salt), triclopyr esters and salts, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, vernolate, xylachlor, and salts, choline salts, esters, optically active isomers and mixtures thereof.

The compositions described herein can be used in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet acid, cloquintocet (mexyl), cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil, R29148, 1-[4-(N-(2-methoxybenzoyl)sulfamoyl)phenyl]-3-methylurea, metcamifen, and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity. The safeners can be used in corn or maize, sorghum, turf, rice, cereals, wheat and barley settings. The safener can be cloquintocet acid or cloquintocet-mexyl, or isoxadifen or isoxadifen-ethyl. Cloquintocet is utilized to antagonize harmful effects of the compositions primarily on rice and cereals, whereas isoxadifen can be utilized to antagonize harmful effects of the compositions primarily in corn, maize, sorghum and turf.

The compositions provided herein can further include one or more agriculturally acceptable adjuvants or carriers. Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application. The adjuvants or carriers can be solids, such as, for example, dusts, granules, water-dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. Additionally, the adjuvants or carriers can also be provided as a pre-mix or tank mixed.

Suitable agricultural adjuvants and carriers include, but are not limited to, crop oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C₉-C₁₁ alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C₁₂-C₁₆) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate+urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99.

Liquid carriers that can be used in the compositions and methods described herein include water and organic solvents. Examples of useful organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like. Specific organic solvents include, but are not limited to toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. Water is useful as a carrier for the dilution of concentrates.

Suitable solid carriers include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, cellulose, and the like.

The compositions described herein may further include one or more surface-active agents. Such surface-active agents can be used in both solid and liquid compositions, and can be designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants which may also be used in the present formulations are described, inter alia, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, N.J., 1998 and in Encyclopedia of Surfactants, Vol. I-III, Chemical Publishing Co., New York, 1980-81. Surface-active agents include, but are not limited to salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-Cis ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C₁₆ ethoxylate; soaps, such as sodium stearate; alkylnaphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseed/canola oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils, e.g., methyl esters. These materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.

Other additives useful in the compositions provided herein include, but are not limited to, compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.

Methods

Methods of using the compositions described herein are also provided. The methods comprise contacting undesirable vegetation with a composition as described herein to prevent the emergence or growth of vegetation, particularly undesirable vegetation. The composition can be applied at an application rate from about 2 grams active ingredient per hectare (g ai/ha) to about 400 g ai/ha based on the total amount of active ingredients in the composition. Alternatively, the composition can be applied at an application rate from about 3 g ai/ha to about 350 g ai/ha based on the total amount of active ingredients in the composition, at an application rate from about 4 g ai/ha to about 325 g ai/ha based on the total amount of active ingredients in the composition, at an application rate from about 7 g ai/ha to about 300 g ai/ha based on the total amount of active ingredients in the composition, at an application rate from about 10 g ai/ha to about 250 g ai/ha based on the total amount of active ingredients in the composition, at an application rate from about 15 g ai/ha to about 225 g ai/ha based on the total amount of active ingredients in the composition, at an application rate from about 20 g ai/ha to about 200 g ai/ha based on the total amount of active ingredients in the composition, at an application rate from about 25 g ai/ha to about 175 g ai/ha based on the total amount of active ingredients in the composition, or at an application rate from about 30 g ai/ha to about 150 g ai/ha based on the total amount of active ingredients in the composition.

In the methods described herein, the components of the mixtures described herein can be applied either separately, sequentially, tank-mixed, or as part of a multipart herbicidal system. Alternatively, the components may be formulated together (e.g., in the same formulation) or separately (e.g., in separate formulations) and applied simultaneously. Also, one or more components may be formulated separately and the components applied sequentially. For example, each component can be formulated separately and the components applied sequentially. The time period between applications can vary, for example, from 1, 5, 10, 15, 30, or 45 minutes or longer; 1, 2, 4, 6, 8, 10, or 12 hours or longer; or 1, 2, 3, 4, 5, 6, or 7 days or longer.

Methods of application useful in the methods described herein include, but are not limited to, applications to the vegetation or locus thereof, e.g., application to the area adjacent to the vegetation, such as soil and/or water, as well as pre-emergence, post-emergence, and foliar (broadcast, directed, banded, spot, mechanical, over-the-top, or rescue), and in-water applications (emerged and submerged vegetation, broadcast, spot, mechanical, water-injected, granular broadcast, granular spot, shaker bottle, or stream spray) via hand, backpack, machine, tractor, or aerial (airplane and helicopter) application methods.

The compositions described herein can exhibit unexpected activity against a variety of weed types. For example, the combination of the compound of formula (I) or salt or ester thereof plus tembotrione in a ratio of about 1:200 to about 200:1 exhibits greater than about 5, 6, 7, 8, 9, 10, 11, 13, 15, 18, 20, 22, 24, 25, 30, 35, 40, 45, 50, 55, or 60% control compared to the sum of the activity of the individual active ingredients in the compositions when used separately at 21 days after application (DAA).

The compositions described herein can exhibit unexpected activity against a variety of weed types. For example, the combination of the compound of formula (I) or salt or ester thereof plus topramezone in a ratio of about 1:100 to about 100:1 exhibits greater than about 5, 6, 7, 8, 9, 10, 11, 13, 15, 18, 20, 22, 24, 25, 30, 35, 40, 45, 50, 55, or 60% control compared to the the sum of the activity of the individual active ingredients in the compositions when used separately at 21 days after application (DAA).

The compositions described herein exhibit unexpected activity as defined by the efficacy values defined above against a variety of weed types or crops, including but not limited to, Brassica napus napus (winter rape), Chenpodium album L. (common lambsquarters), Cirsium arvense (L.) Scop. (Canada thistle), Galium aparine L. (catchweed bedstraw), Kochia scoparia (L.) Schrad. (kochia), Lamium purpureum L. (purple deadnettle), Matricaria recutita L. (wild chamomile), Papaver rhoeas L. (common poppy), Salsola tragus L. (Russian thistle), Sinapis arvensis L. (wild mustard), Stellaria media (common chickweed), Veronica persica Poir. (Persian speedwell), and Viola tricolor L. (wild violet).

The methods provided herein can be used to control undesirable vegetation such as grass, broadleaf and sedge weeds, in crops including, but not limited to, corn, maize, sorghum, direct-seeded, water-seeded and transplanted rice, wheat, durum, barley, millet, oats, rye, triticale, teff, fonio, spelt, and canary grass; pseudocereals including, but not limited to, quinoa, amaranth, buckwheat, kañiwa, and pitseed goosefoot; other crops including but not limited to, soybean, cotton, canola, sugar beet, pineapple, oilseed rape; pastures, grasslands, rangelands, and fallowland; turf, tree and vine orchards; plantation crops; aquatics; rights-of-way; and industrial vegetation management (IVM). The compositions and methods provided herein are especially useful for the control of undesirable vegetation in corn crops (field corn, field corn grown for seed, popcorn sweet corn), sorghum, and any other crops that are naturally tolerant or contain herbicide tolerant traits to these active ingredients.

The compositions and methods may be used in controlling undesirable vegetation in crops possessing agronomic stress tolerance (including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH), pest tolerance (including but not limited to insects, fungi and pathogens) and crop improvement traits (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture).

In some embodiments, the compositions and methods provided herein are utilized to control undesirable vegetation consisting of grass, broadleaf and sedge weeds. In certain embodiments, the compositions and methods provided herein are utilized to control undesirable vegetation including Amarantus, Chenopodium, Echinochloa, Ipomoea, Setaria, and Xanthium.

In some embodiments, the combination of compound (I) or agriculturally acceptable ester or salt thereof and tembotrione and/or topramezone can be used to control barnyardgrass (Echinochloa crus-galli (L.) Beauv., ECHCG common lambsquarter (Chenopodium album L.), ivyleaf morningglory (Ipomoea hederacea Jacq., IPOHE), green foxtail (Setaria viridis (L.) Beauv., SETVI), Palmer amaranth (Amaranthus palmeri, AMAPA), redroot pigweed (Amaranthus retroflexus, AMARE), and common cocklebur (Xanthium strumarium L.).

In the methods described herein, the compositions can be used to control undesirable vegetation in row crops. Examples of the types of undesirable vegetation that can be controlled in row crops using the methods and compositions described herein include Alopecurus myosuroides Huds. (blackgrass, ALOMY), Amaranthus palmeri (Palmer amaranth, AMAPA), Amaranthus retroflexus (redroot pigweed, AMARE), Avena fatua L. (wild oat, AVEFA), Brachiaria platyphylla (Groseb.) Nash (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild-proso millet, PANMI), Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL), Ambrosia psilostachya DC. (western ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Asclepias syriaca L. (common milkweed, ASCSY), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE), Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Erigeron bonariensis L. (hairy fleabane, ERIBO), Erigeron canadensis L. (Canadian fleabane, ERICA), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (smallflower morningglory, IAQTA), Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (white morningglory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), or Xanthium strumarium L. (common cocklebur, XANST).

In the methods described herein, the compositions can be used to control undesirable vegetation in cereals. Examples of the types of undesirable vegetation that can be controlled in cereals using the methods and compositions described herein include Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Lolium rigidum (rigid ryegrass, LOLRI), Lolium multiflorum subsp. Gaudini (annual ryegrass, LOLMG), Phalaris minor Retz. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POAAN), Setaria pumila (Poir.) Roemer & J. A. Schultes (yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthus retroflexus (redroot pigweed, AMARE), Chenopodium album (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureum L. (purple deadnettle, LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT), Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Sinapis arvensis (wild mustard, SINAR), Stellaria media (L.) Vill. (common chickweed, STEME), Veronica hederifolia (ivy-leaved speedwell, VERHE), Veronica persica Poir. (Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).

In the methods described herein, the compositions can be used to control undesirable vegetation in rice. Examples of the types of undesirable vegetation that can be controlled in rice using the methods and compositions described herein include Brachiaria platyphylla (Groseb.) Nash (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam) Gray (bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon sprangletop, LEFPA), Panicum dichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Cyperus difformis L. (small-flower flatsedge, CYPDI), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI), Schoenoplectus juncoides Roxb. (Japanese bulrush, SPCJU), Schoenoplectus maritimus L. (sea clubrush, SCPMA), Schoenoplectus mucronatus L. (ricefield bulrush, SCPMU), Aeschynomene species, (jointvetch, AESSS), Alternanthera philoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alisma plantago-aquatica L. (common waterplantain, ALSPA), Amaranthus species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Eclipta alba (L.) Hassk. (American false daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (ducksalad, HETLI), Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE), Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Lindemia dubia (L.) Pennell (low false pimpernel, LIDDU), Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth (monochoria, MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L. (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb, POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species (arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).

In some embodiments, the methods provided herein are utilized to control undesirable vegetation in turf. In certain embodiments, the undesirable vegetation is Bellis perennis L. (English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Diodia virginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata L. (dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamium amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L. (broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhorn/narrowleaf plantain, PLALA), Phyllanthus urinaria L. (chamberbitter, PYLTE), Rumex obtusifolius L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum officinale G. H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Viola species (wild violet, VIOSS).

In the methods described herein, the compositions can be used to control undesirable vegetation in range and pasture. Examples of the types of undesirable vegetation that can be controlled in range and pasture using the methods and compositions described herein include Ambrosia artemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam (spotted knapweed, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhorn plantain, PLALA), Rumex obtusifolius L. (broadleaf dock, RUMOB), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum officinale G. H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).

The compositions and methods described herein can also be used to control undesirable vegetation in herbicide-tolerant crops including, but not limited to, glyphosate-tolerant-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-tolerant-, glufosinate-tolerant-, glutamine synthetase inhibitor-tolerant-, dicamba-tolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-, auxin-tolerant-, auxin transport inhibitor-tolerant, aryloxyphenoxypropionate-tolerant-, cyclohexanedione-tolerant-, phenylpyrazoline-tolerant-, acetyl CoA carboxylase (ACCase) inhibitor-tolerant-, imidazolinone-tolerant-, sulfonylurea-tolerant-, pyrimidinylthiobenzoate-tolerant-, triazolopyrimidine-tolerant-, sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-, phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesis inhibitor-tolerant-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-tolerant-, protoporphyrinogen oxidase (PPO) inhibitor-tolerant-, cellulose biosynthesis inhibitor-tolerant-, mitosis inhibitor-tolerant-, microtubule inhibitor-tolerant-, very long chain fatty acid inhibitor-tolerant-, fatty acid and lipid biosynthesis inhibitor-tolerant-, photosystem I inhibitor-tolerant-, photosystem II inhibitor-tolerant-, triazine-tolerant-, and bromoxynil-tolerant-crops (such as, but not limited to, soybean, cotton, canola/oilseed rape, rice, cereals, corn/maize, sorghum, sunflower, sugar beet, sugarcane, turf, wheat, barley, etc.), for example, in conjunction with glyphosate, EPSP synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACCase inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil. The compositions and methods may be used in controlling undesirable vegetation in crops possessing multiple or stacked traits conferring tolerance to single or multiple chemistries and/or inhibitors of single or multiple modes of action. The compositions and methods may be used in controlling undesirable vegetation in crops possessing agronomic stress tolerance (including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH), pest tolerance (including but not limited to insects, fungi and pathogens) and crop improvement traits (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture).

The described compositions and methods and following examples are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations with respect to the compositions and methods described herein will be apparent to a person of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.

EXAMPLES

Results in Example I are from greenhouse trials.

Example I. Evaluation of Post-Emergence Foliar-Applied Herbicidal Mixtures for Weed Control in Corn

Seeds of the desired test plant species were planted in a potting media, Metro-mix 360, a peat based potting soil. Metro-mix consists of 35 to 45% specially processed coconutcoir pith, 10 to 20% horticultural grade vermiculite, 15 to 25% processed ash bark, 20 to 30% choice Canadian sphagnum peat moss and proprietary nutrients and other ingredients. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical treatment was applied. The plants were grown for 8-16 days in a greenhouse with an approximate 14 h photoperiod which was maintained at about 29° C. during the day and 26° C. during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg and iron chelate) were applied in the irrigation solution as needed and water was added on a regular basis. Supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were sprayed when they reached the second through fourth true leaf stage.

Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (II), formulated as an SC (suspension concentrate), GF-2978 containing 125.8 g ai/L of active ingredient, and various herbicidal components alone and in combination. The benzyl ester of formula (II) was applied on an active ingredient basis.

Other herbicidal components were applied on an active ingredient basis and included 4-hydroxyphenyl pyruvate dioxygenase (HPPD)-inhibiting herbicides tembotrione formulated as Laudis, an SC formulation containing 420 g ai/L of tembotrione, or topramezone formulated as Armezon, an SC formulation containing 335.8 g ai/L of topramezone. All treatments were applied with Prime Oil, (crop oil concentrate) at 1% v/v.

Treatment requirements were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, for a 30 ml volume based off of an application rate of 200 L/ha. Appropriate amounts of formulated product as calculated by the software package ARM8 (Gylling Data Management Inc.) were added to 60 ml glass vials and diluted with Indianapolis tap water and Prime Oil at 1% v/v. Treatments were applied with Generation III Research Track-Sprayer manufactured by DeVries Manufacturing in Hollandale, Minn., USA, located in building 306, room E1-483, at the Dow AgroSciences Global headquarters in Indianapolis, Ind. US. The track sprayer was calibrated to deliver 200 L/ha utilizing an 8003E even fan spray nozzle at 40 psi (276 kPa) at a speed of 2 mph (3.25 km/hr) and a spray height of 18 to 20 inches (46 to 50 cm) above average plant canopy height.

The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After approximately 3 weeks, the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill. The Colby method was used to determine the herbicidal effects expected from the mixtures.

In some embodiments, the activity of the mixtures is greater than the sum of the activity of the individual active ingredients when applied separately.

The compounds tested, application rates employed, plant species tested, and results are given in Tables 1-2.

TABLE 1 Herbicidal Activity of Foliar-Applied Compound II and Tembotrione Herbicidal Compositions on Various Weeds Visual Weed Control (%) - 12 DAA Compound II Tembotrione AMAPA gai/ha gai/ha Obs Exp 2.5 0 75 — 5 0 73.33 — 15 0 80 — 0 5.75 44.33 — 0 11.5 50 — 0 23 66 — 2.5 5.75 95.0 85.8 2.5 23 99.3 91.6 5 23 100.0 90.9 15 11.5 100.0 89.6 15 5.75 100.0 88.6 Visual Weed Control (%) - 12 DAA Compound II Tembotrione AMARE gai/ha gai/ha Obs Exp 2.5 0 61.25 — 7.5 0 75 — 0 46 43.75 — 2.5 46 89.3 77.9 7.5 46 100.0 85.9 Visual Weed Control (%) - 5 DAA Compound II Tembotrione ECHCG gai/ha gai/ha Obs Exp 2.5 0 22.5 — 0 46 57.5 — 2.5 46 75.0 67.0

TABLE 2 Herbicidal Activity of Foliar-Applied Compound II and Topramezone Herbicid Compositions on Various Weeds Visual Weed Control (%) - 12 DAA Compound II Topramezone AMAPA gai/ha gai/ha Obs Exp 2.5 0 75 — 5 0 73.33 — 7.5 0 85 — 15 0 80 — 0 3 86.67 — 0 6 75 — 2.5 6 99.3 93.3 5 3 99.7 96.7 7.5 6 100.0 96.3 15 3 100.0 97.7 Visual Weed Control (%) - 12 DAA Compound II Topramezone AMARE gai/ha gai/ha Obs Exp 2.5 0 61.25 — 5 0 65.75 — 7.5 0 75 — 0 6 52.5 — 0 12 77.5 — 2.5 6 99.5 81.3 2.5 12 98.0 91.3 5 6 99.0 83.5 5 12 100.0 92.3 7.5 6 99.8 88.1 Visual Weed Control (%) - 5 DAA Compound II Topramezone AMARE gai/ha gai/ha Obs Exp 15 0 73 — 0 24 50.75 — 15 24 90.0 86.8 Visual Weed Control (%) - 12 DAA Compound II Topramezone ECHCG gai/ha gai/ha Obs Exp 5 0 61.25 — 7.5 0 70.75 — 0 3 0 — 0 6 1.25 — 0 12 36.25 — 5 3 66.3 61.3 5 6 72.5 61.7 5 12 91.3 75.4 7.5 3 78.3 70.8 7.5 6 80.0 71.2 7.5 12 89.5 81.1 Visual Weed Control (%) - 5 DAA Compound II Topramezone ECHCG gai/ha Gaiha Obs Exp 2.5 0 22.5 — 5 0 53.75 — 7.5 0 55 — 15 0 65 — 0 3 0.75 — 0 6 6.25 — 0 24 51.25 — 2.5 3 32.5 23.0 2.5 24 78.3 62.1 7.5 3 61.8 55.3 7.5 6 75.0 57.8 15 3 70.5 65.3 15 6 71.8 67.2 Visual Weed Control (%) - 5 DAA Compound II Topramezone IPOHE gai/ha gaiha Obs Exp 2.5 0 51.25 — 5 0 62.5 — 7.5 0 61.25 — 15 0 55.75 — 0 3 6.25 — 0 6 6.25 — 0 12 8.75 — 0 24 33.25 — 2.5 3 61.3 54.3 2.5 6 73.8 54.3 2.5 12 66.3 55.5 2.5 24 76.3 67.4 5 12 70.8 65.8 5 24 83.0 74.8 7.5 6 76.5 63.6 7.5 12 77.5 64.6 7.5 24 81.3 74.1 15 3 73.3 58.7 15 6 80.5 58.7 15 12 83.0 59.7 15 24 79.0 71.0

IPOHE Ipomoea hederacea (L.) Jacq. morningglory, ivyleaf SETVI Setaria viridis (L.) Beauv. foxtail, green XANST Xanthium strumarium L. cocklebur, common AMAPA Amaranthus palmeri Palmer amaranth AMARE Amaranthus retroflexus redroot pigweed CHEAL Chenopodium album L. common lambsquarters ECHCG Echinochloa crusgalli (L.) Beauv. barnyardgrass gae/ha=grams acid equivalent per hectareAPA gai/ha=grams active ingredient per hectare Obs=observed value Exp=expected value as calculated by Colby's equation DAA=days after application 

What is claimed is:
 1. A herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester thereof, and (b) tembotrione and/or topramezone.
 2. The composition of claim 1, wherein the herbicidal composition is for use in corn crops and sorgum.
 3. The composition of claim 2, wherein the corn crops include field corn, field corn grown for seed, popcorn, and sweet corn.
 4. The composition of claim 1, wherein (a) is a benzyl ester of the compound of formula (I).
 5. The composition of claim 1, further comprising a herbicide safener.
 6. The composition of claim 1, wherein the weight ratio of the compound of formula (I) or an agriculturally acceptable salt or ester thereof to tembotrione is from about 1:200 to 200:1.
 7. The composition of claim 1, wherein the weight ratio of the compound of formula (I) or an agriculturally acceptable salt or ester thereof to topramezone is from about 1:200 to 200:1.
 8. The composition of claim 1, further comprising an agriculturally acceptable adjuvant or carrier.
 9. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation with a herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I)

or an agriculturally acceptable salt or ester thereof and (b) tembotrione and/or topramezone.
 10. The method of claim 9, wherein (a) is a benzyl ester of the compound of formula (I).
 11. The method of claim 9, wherein the herbicidal composition further comprises a safener.
 12. The method of claim 9, wherein the weight ratio of the compound of formula (I) or an agriculturally acceptable salt or ester thereof to tembotrione is from about 1:200 to 200:1.
 13. The method of claim 9, wherein the weight ratio of the compound of formula (I) or an agriculturally acceptable salt or ester thereof to topramezone is from about 1:200 to 200:1.
 14. The method of claim 9, wherein the herbicidal composition further comprises an agriculturally acceptable adjuvant or carrier.
 15. The method of claim 9, wherein the undesirable vegetation is controlled in corn, maize, sorghum, direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) or rights-of-way (ROW).
 16. The method of claim 9, wherein the undesirable vegetation is controlled in corn crops such as field corn, field corn grown for seed, popcorn, and sweet corn, and sorghum.
 17. The method of claim 9, wherein the (a) and (b) are applied pre-emergently to the weed or the crop.
 18. The method of claim 9, wherein the undesirable vegetation is controlled in glyphosate-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-, triazine-, or bromoxynil-tolerant crops.
 19. The method of claim 9, wherein the undesirable vegetation comprises a herbicide resistant or tolerant weed.
 20. The method of claim 19, wherein the resistant or tolerant weed is a biotype resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall, or organoarsenicals. 